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  • 1.
    Buitrago, Elina
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient and Selective Hydrosilylation of Carbonyls Catalyzed by Iron Acetate and N-Hydroxyethylimidazolium Salts2012Ingår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, nr 1, s. 217-222Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Aromatic aldehydes, along with aryl alkyl, heteroaryl alkyl, and dialkyl ketones were efficiently reduced to their corresponding primary and secondary alcohols, respectively, in high yields, using the commercially available and inexpensive polymeric silane, polymethylhydrosiloxane (PMHS), as reducing agent. The reaction is catalyzed by in situ generated iron complexes containing hydroxyethyl-functionalized NHC ligands. Turnover frequencies up to 600 h−1 were obtained

  • 2.
    Lundberg, Helena
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Direct Amide Coupling of Non-activated Carboxylic Acids and Amines Catalysed by Zirconium(IV) Chloride2012Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, nr 13, s. 3822-3826Artikel i tidskrift (Refereegranskat)
  • 3.
    Lundberg, Helena
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Titanium(IV) Isopropoxide as an Efficient Catalyst for Direct Amidation of Nonactivated Carboxylic Acids2012Ingår i: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 23, nr 15, s. 2201-2204Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Secondary and tertiary amides are formed in high yields, in an efficient and environmentally benign titanium(IV) isopropoxide catalyzed direct amidation of carboxylic acids with primary and secondary amines.

  • 4.
    Lundberg, Helena
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Selander, Nicklas
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic amide formation from non-activated carboxylic acids and amines2014Ingår i: Chemical Society Reviews, ISSN 0306-0012, E-ISSN 1460-4744, Vol. 43, nr 8, s. 2714-2742Artikel, forskningsöversikt (Refereegranskat)
    Abstract [en]

    The amide functionality is found in a wide variety of biological and synthetic structures such as proteins, polymers, pesticides and pharmaceuticals. Due to the fact that synthetic amides are still mainly produced by the aid of coupling reagents with poor atom-economy, the direct catalytic formation of amides from carboxylic acids and amines has become a field of emerging importance. A general, efficient and selective catalytic method for this transformation would meet well with the increasing demands for green chemistry procedures. This review covers catalytic and synthetically relevant methods for direct condensation of carboxylic acids and amines. A comprehensive overview of homogeneous and heterogeneous catalytic methods is presented, covering biocatalysts, Lewis acid catalysts based on boron and metals as well an assortment of other types of catalysts.

  • 5.
    Lundberg, Helena
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Zhang, Jiji
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Algarra, Andrés G.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Universidad de Cádiz, Spain.
    Himo, Fahmi
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Umeå University, Sweden.
    Mechanistic Elucidation of Zirconium-Catalyzed Direct Amidation2017Ingår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 139, nr 6, s. 2286-2295Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The mechanism of the zirconium-catalyzed condensation of carboxylic acids and amines for direct formation of amides was studied using kinetics, NMR spectroscopy, and DFT calculations. The reaction is found to be first order with respect to the catalyst and has a positive rate dependence on amine concentration. A negative rate dependence on carboxylic acid concentration is observed along with S-shaped kinetic profiles under certain conditions, which is consistent with the formation of reversible off-cycle species. Kinetic experiments using reaction progress kinetic analysis protocols demonstrate that inhibition of the catalyst by the amide product can be avoided using a high amine concentration. These insights led to the design of a reaction protocol with improved yields and a decrease in catalyst loading. NMR spectroscopy provides important details of the nature of the zirconium catalyst and serves as the starting point for a theoretical study of the catalytic cycle using DFT calculations. These studies indicate that a dinuclear zirconium species can catalyze the reaction with feasible energy barriers. The amine is proposed to perform a nucleophilic attack at a terminal eta(2)-carboxylate ligand of the zirconium catalyst, followed by a C-O bond cleavage step, with an intermediate proton transfer from nitrogen to oxygen facilitated by an additional equivalent of amine. In addition, the DFT calculations reproduce experimentally observed effects on reaction rate, induced by electronically different substituents on the carboxylic acid.

  • 6. Margalef, Jèssica
    et al.
    Slagbrand, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Umeå University, Sweden.
    Diéguez, Montserrat
    Pàmies, Oscar
    Third-Generation Amino Acid Furanoside-Based Ligands from d-Mannose for the Asymmetric Transfer Hydrogenation of Ketones: Catalysts with an Exceptionally Wide Substrate Scope2016Ingår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 358, nr 24, s. 4006-4018Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A modular ligand library of -amino acid hydroxyamides and thioamides was prepared from 10 different N-tert-butyloxycarbonyl-protected -amino acids and three different amino alcohols derived from 2,3-O-isopropylidene--d-mannofuranoside. The ligand library was evaluated in the half-sandwich ruthenium- and rhodium-catalyzed asymmetric transfer hydrogenation of a wide array of ketone substrates, including simple as well as sterically demanding aryl alkyl ketones, aryl fluoroalkyl ketones, heteroaromatic alkyl ketones, aliphatic, conjugated and propargylic ketones. Under the optimized reaction conditions, secondary alcohols were obtained in high yields and in enantioselectivities up to >99%. The choice of ligand/catalyst allowed for the generation of both enantiomers of the secondary alcohols, where the ruthenium-hydroxyamide and the rhodium-thioamide catalysts act complementarily towards each other. The catalytic systems were also evaluated in the tandem isomerization/asymmetric transfer hydrogenation of racemic allylic alcohols to yield enantiomerically enriched saturated secondary alcohols in up to 98% ee. Furthermore, the catalytic tandem -alkylation/asymmetric transfer hydrogenation of acetophenones and 3-acetylpyridine with primary alcohols as alkylating and reducing agents was studied. Secondary alcohols containing an elongated alkyl chain were obtained in up to 92% ee.

  • 7.
    Rabten, Wangchuk
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kärkäs, Markus D.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Torbjörn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Chen, Hong
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Liao, Rong-Zhen
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sun, Junliang
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Siegbahn, Per E. M.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Andersson, Pher G.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic Water Oxidation by a Molecular Ruthenium Complex: Unexpected Generation of a Single-Site Water Oxidation Catalyst2015Ingår i: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 54, nr 10, s. 4611-4620Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The increasing energy demand calls for the development of sustainable energy conversion processes. Here, the splitting of H2O to O-2 and H-2, or related fuels, constitutes an excellent example of solar-to-fuel conversion schemes. The critical component in such schemes has proven to be the catalyst responsible for mediating the four-electron oxidation of H2O to O-2. Herein, we report on the unexpected formation of a single-site Ru complex from a ligand envisioned to accommodate two metal centers. Surprising N-N bond cleavage of the designed dinuclear ligand during metal complexation resulted in a single-site Ru complex carrying a carboxylate amide motif. This ligand lowered the redox potential of the Ru complex sufficiently to permit H2O oxidation to be carried out by the mild one-electron oxidant [Ru(bpy)(3)](3+) (bpy = 2,2'-bipyridine). The work thus highlights that strongly electron-donating ligands are important elements in the design of novel, efficient H2O :oxidation catalysts.

  • 8.
    Shatskiy, Andrey
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kivijärvi, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lundberg, Helena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Propargylic Ketones2015Ingår i: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 7, nr 23, s. 3818-3821Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The asymmetric transfer hydrogenation of alpha,beta-propargyl ketones catalyzed by an in situ formed ruthenium-hydroxyamide complex was explored. The acetylenic alcohols were isolated in good to excellent yields with excellent ee values (typically >90%) after short reaction times at room temperature.

  • 9.
    Slagbrand, Tove
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kervefors, Gabriella
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Umeå University, Sweden.
    An Efficient One-pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides2017Ingår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 359, nr 11, s. 1990-1995Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A Mo(CO)(6) (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated.

  • 10.
    Slagbrand, Tove
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Volkov, Alexey
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Trillo, Paz
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Umeå University, Sweden.
    Transformation of Amides into Highly Functionalized Triazolines2017Ingår i: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 7, nr 3, s. 1771-1775Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Triazoles and triazolines are important classes of heterocyclic compounds known to exhibit biological activity. Significant focus has been given to the development of synthetic approaches for the preparation of triazoles, and they are today easily obtainable through a large variety of protocols. The number of synthetic procedures for the formation of triazolines, on the other hand, is limited and further research in this field is required. The protocol presented here gives access to a broad scope of 1,4,5-substituted 1,2,3-triazolines through a one-pot transformation of carboxamides. The two-step procedure involves a Mo(CO)6-catalyzed reduction of tertiary amides to afford the corresponding enamines, followed by in situ cycloaddition of organic azides to form triazolines. The amide reduction is chemoselective and allows for a wide variety of functional groups such as esters, ketones, aldehydes, and imines to be tolerated. Furthermore, a modification of this one-pot procedure gives access to the corresponding triazoles. The chemically stable amide functionality is demonstrated to be an efficient synthetic handle for the formation of highly substituted triazolines or triazoles.

  • 11.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic Formation of Amides2014Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
    Abstract [en]

    The amide functionality is a highly important chemical bond, found in a great number of synthetic products such as pharmaceuticals, polymers and agrochemicals. The focus of this thesis has been directed towards efficient, mild and environmentally friendly methods for amide formations. The first part is devoted to the investigation of a Lewis acid catalyzed protocol for direct condensation of non-activated carboxylic acids and amines. ZrCl4 was found to be a highly active catalyst and a low catalytic loading enabled for high yields of secondary and tertiary amides under relatively mild conditions. The second part of the thesis describes our investigations towards a catalytic method for primary amides. We demonstrated that the transformation was feasible by performing minor alterations to the previous Lewis acid based procedure. A variety of primary amides could be obtained in high yields by the use of carbamates, as a non-gaseous source of ammonia in combination with carboxylic acids and catalytic amounts of TiCl4 or ZrCl4. Furthermore, the protocol was extended to include catalytic formation of N,N-dimethylamides from non-activated carboxylic acids.

    The use of immobilized metal nanoparticles as heterogeneous catalysts has emerged as a highly investigated research area. The final chapter of this thesis deals with the successful application of an immobilized Pd nanocatalyst for amide formation via the aminocarbonylation reaction of aryl iodides. The Pd0-AmP-MCF catalyst was found to operate through a “release and catch” mechanism, in which PdII species were released into the solution and then re-deposited onto the support after completion of the reaction. It was discovered that the combination of aryl halide and amine was the cause of the leaching, and furthermore that the homogeneous Pd species catalyzed the aminocarbonylation reaction. A selection of aryl iodides were evaluated using 2 mol% of Pd0-AmP-MCF under atmospheric pressure of CO, and the corresponding amides were obtained in good to high yields.

  • 12.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Selective Transition Metal Catalyzed Transformations – Reductions and Amidations2012Licentiatavhandling, sammanläggning (Övrigt vetenskapligt)
  • 13.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Asymmetric transfer hydrogenation of ketones catalyzed by rhodium complexes containing amino acid triazole ligands2010Ingår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 8, nr 20, s. 4536-4539Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Active and selective catalysts for the asymmetric reduction of ketones, under transfer hydrogenation conditions, were obtained by combining [RhCl2Cp*](2), with a series of L-amino acid thioamide ligands functionalized with 1,2,3-triazoles. The obtained secondary alcohol products were formed with up to 93% ee.

  • 14.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ruthenium catalyzed asymmetric transfer hydrogenation employing novel bidentate abnormal NHC ligands2011Konferensbidrag (Övrigt vetenskapligt)
    Abstract [en]

    N-Heterocyclic carbenes (NHCs) have been successfully employed as ligands in iridium, rhodium and ruthenium catalyzed transfer hydrogenation reactions. However, there are few reports on the use of catalysts containing chiral NHC ligands for this particular transformation. Furthermore, to the best of our knowledge there are no reports on the use of catalysts based on abnormal NHC ligands in asymmetric transfer hydrogenations. In this work we have prepared novel chiral bidentate NHCs that have the potential for an abnormal binding mode to transitionmetals. Ruthenium complexes of these ligands were employed in the asymmetric transfer hydrogenation of ketones in 2-propanol.

  • 15.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lundberg, Helena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Direct Catalytic Formation of Primary and Tertiary Amides from Non-Activated Carboxylic Acids, Employing Carbamates as Amine Source2012Ingår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, nr 13, s. 2531-2536Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The operationally simple titanium(IV)- or zirconium(IV)-catalyzed direct amidation of non-activated carboxylic acids with ammonium carbamates generates primary, and tertiary N,N-dimethyl-substituted amides in good to excellent yields.

  • 16.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lundberg, Helena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kivijärvi, Tove
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Zirconium(IV) Chloride Catalyzed Amide Formation from Carboxylic Acids and Amines: N-Benzyl-2-(phenylthio)acetamide and (S)-tert-butyl-2-(benzylcarbamoyl)pyrrolidine-1-carboxylateManuskript (preprint) (Övrigt vetenskapligt)
  • 17.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lundberg, Helena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kivijärvi, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hans, Adolfsson
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Zirconium(IV) chloride catalyzed amide formation from carboxylic acids and amines: N-Benzyl-2-(phenylthio)acetamide and (S)-tert-butyl 2-(benzylcarbamoyl)pyrrolidine-1-carboxylateIngår i: Organic Syntheses, ISSN 0078-6209Artikel i tidskrift (Refereegranskat)
  • 18.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Stridfeldt, Elin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lundberg, Helena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Olofsson, Berit
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Stellenbosch University, South Africa.
    Metal-Free N-Arylation of Secondary Amides at Room Temperature2015Ingår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, nr 11, s. 2688-2691Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.

  • 19.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Verho, Oscar
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Gustafson, Karl P. J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tai, Cheuk-Wai
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient Palladium-Catalyzed Aminocarbonylation of Aryl Iodides Using Palladium Nanoparticles Dispersed on Siliceous Mesocellular Foam2014Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, nr 20, s. 5885-5889Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A highly dispersed nanopalladium catalyst supported on mesocellular foam (MCF), was successfully used in the heterogeneous catalysis of aminocarbonylation reactions. During the preliminary evaluation of this catalyst it was discovered that the supported palladium nanoparticles exhibited a “release and catch” effect, meaning that a minor amount of the heterogeneous palladium became soluble and catalyzed the reaction, after which it re-deposited onto the support.

  • 20.
    Tinnis, Fredrik
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Volkov, Alexey
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Slagbrand, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Chemoselective Reduction of Tertiary Amides under Thermal Control: Formation of either Aldehydes or Amines2016Ingår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, nr 14, s. 4562-4566Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The chemoselective reduction of amides in the presence of other more reactive reducible functional groups is a highly challenging transformation, and successful examples thereof are most valuable in synthetic organic chemistry. Only a limited number of systems have demonstrated the chemoselective reduction of amides over ketones. Until now, the aldehyde functionality has not been shown to be compatible in any catalytic reduction protocol. Described herein is a [Mo(CO)6]-catalyzed protocol with an unprecedented chemoselectivity and allows for the reduction of amides in the presence of aldehydes and imines. Furthermore, the system proved to be tunable by variation of the temperature, which enabled for either C−O or C−N bond cleavage that ultimately led to the isolation of both amines and aldehydes, respectively, in high chemical yields.

  • 21.
    Trillo, Paz
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Slagbrand, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Umeå University, Sweden.
    Facile preparation of pyrimidinediones and thioacrylamides via reductive functionalization of amides2017Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 53, nr 65, s. 9159-9162Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The development of an efficient protocol for the reductive functionalization of amides into pyrimidinediones and amino-substituted thioacrylamides is presented. Enamines are generated in a highly chemoselective amide hydrosilylation reaction catalyzed by molybdenum hexacarbonyl in combination with 1,1,3,3-tetramethyldisiloxane. The direct addition of either isocyanate or isothiocyanate generates the corresponding pyrimidinediones and 3-aminothioacrylamides in high yields.

  • 22.
    Trillo, Paz
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Slagbrand, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Umeå University, Sweden.
    Mild Reductive Functionalization of Amides into N-Sulfonylformamidines2017Ingår i: ChemistryOpen, ISSN 2191-1363, Vol. 6, s. 484-487Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The development of a protocol for the reductive functionalization of amides into N-sulfonylformamidines is reported. The one-pot procedure is based on a mild catalytic reduction of tertiary amides into the corresponding enamines by the use of Mo(CO)6 (molybdenum hexacarbonyl) and TMDS (1,1,3,3-tetramethyldisiloxane). The formed enamines were allowed to react with sulfonyl azides to give the target compounds in moderate to good yields.

  • 23.
    Volkov, Alexey
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions2014Ingår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, nr 3, s. 680-683Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Tertiary amides are efficiently reduced to their corresponding enamines under hydrosilylation conditions, using a transition-metal-free catalytic protocol based on t-BuOK (5 mol %) and (MeO)(3)SiH or (EtO)(3)SiH as the reducing agent. The enamines were formed with high selectivity in good-to-excellent yields.

  • 24.
    Volkov, Alexey
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Slagbrand, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Pershagen, Ida
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mo(CO)6 catalysed chemoselective hydrosilylation of alpha,beta-unsaturated amides for the formation of allylamines2014Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 50, nr 93, s. 14508-14511Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Molybdenum hexacarbonyl (Mo(CO)(6)) was used as an efficient catalyst for the chemoselective reduction of the amide functionality in alpha,beta-unsaturated compounds, under hydrosilylation conditions using 1,1,3,3-tetramethyldisiloxane (TMDS) as the hydride source.

  • 25.
    Volkov, Alexey
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tinnis, Fredrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Stagbrand, Tove
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Trillo, Paz
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Chemoselective reduction of carboxamides2016Ingår i: Chemical Society Reviews, ISSN 0306-0012, E-ISSN 1460-4744, Vol. 45, nr 24, s. 6685-6697Artikel, forskningsöversikt (Refereegranskat)
    Abstract [en]

    The reduction of amides gives access to a wide variety of important compounds such as amines, imines, enamines, nitrites, aldehydes and alcohols. The chemoselective transformation into these functional groups is challenging due to the intrinsic stability of the amide bond; nevertheless, the ability to reduce highly stable carboxamides selectively in the presence of sensitive functional groups is of high synthetic value for academic and industrial chemists. Hydride-based reagents such as LiAlH4 or diboranes are today the most commonly used compounds for amide reductions, and apart from the substantial amount of waste generated using these methods, they lack tolerance to most other functional groups. This tutorial review provides an overview of the recent progress made in the development of chemoselective protocols for amide reduction and gives an insight to their advantages and drawbacks.

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